The application of (S)-1,10-binaphthyl-2,20-diol as NMR chiral solvating agent (CSA) for omeprazole, and three of its analogs (lanso-, panto-, and rabe-prazole) was investigated. The formation of diastereomeric host–guest complexes in solution between the CSA and the racemic substrates produced sufficient NMR signal splitting for the determination of enantiomeric excesses by Hor F-NMR spectroscopy. Using of hydrophobic deuterated solvents was mandatory for obtaining good enantiodiscrimination, thus suggesting the importance of intermolecular hydrogen bonds in the stabilization of the complexes. The method was applied to the fast quantification of the enantiomeric purity of in-process samples of S-omeprazole. Chirality 00:000–000, 2009. VC 2009

The assignment of absolute configuration by NMR

Peroxy natural products

Five new hydroanthraquinone derivatives, tetrahydroaltersolanols C–F (1–4) and dihydroaltersolanol A (5), and five new alterporriol-type anthranoid dimers, alterporriols N–R (12–16), along with seven known analogues (6–11 and 17), were isolated from the culture broth and the mycelia of Alternaria sp. ZJ-2008003, a fungus obtained from a Sarcophyton sp. soft coral collected from the South China Sea. Their structures and the relative configurations were elucidated using comprehensive spectroscopic methods including 1D and 2D NOE spectra as well as single-crystal X-ray crystallography. Compound 13 represents the first isolated alterporriol dimer with a C-4–C-4′ linkage, and the absolute configuration of 4 was determined using the modified Mosher’s method. Compounds 1 and 15 exhibited antiviral activity against the porcine reproductive and respiratory syndrome virus (PRRSV), with IC50 values of 65 and 39 μM, respectively. Compound 14 showed cytotoxic activity against PC-3 and HCT-116 cell lines, with IC50 val...

Bioactive Hydroanthraquinones and Anthraquinone Dimers from a Soft Coral-Derived Alternaria sp. Fungus

An aciduric fungal strain, Penicillium camemberti OUCMDZ-1492, was isolated from an acidic marine niche, mangrove soil and mud, around the roots of Rhizophora apiculata. Six new indole-diterpenoids (1-6), along with five known analogues, emindole SB (7), 21-isopentenylpaxilline (8), paspaline (9), paxilline (10), and dehydroxypaxilline (11), were isolated from the fermentation broth of P. camemberti OUCMDZ-1492 grown at pH 5.0. On the basis of spectroscopic analyses, CD spectra, quantum ECD calculations, and chemical methods, new structures 1-6 were established as 3-deoxo-4b-deoxypaxilline, 4a-demethylpaspaline-4a-carboxylic acid, 4a-demethylpaspaline-3,4,4a-triol, 2'-hydroxypaxilline, 9,10-diisopentenylpaxilline, and (6S,7R,10E,14E)-16-(1H-indol-3-yl)-2,6,10,14-tetramethylhexadeca-2,10,14-triene-6,7-diol, respectively. Compounds 1-3 and 5-10 exhibited significant activity against the H1N1 virus with IC50 values of 28.3, 38.9, 32.2, 73.3, 34.1, 26.2, 6.6, 77.9, and 17.7 μM, respectively. The results showed that 3-oxo, 4b-hydroxy, and 9-isopentenyl substitutions tend to increase the anti-H1N1 activity of hexacyclic indole-diterpenoids.

Indole-Diterpenoids with Anti-H1N1 Activity from the Aciduric Fungus Penicillium camemberti OUCMDZ-1492

Macrocarpals: HIV-RTase inhibitors of Eucalyptus globulus

Anomaly in the modified Mosher's method: Absolute configurations of some marine cembranolides

Three new cembranoids, (+)-isosarcophine (1), (+)-8-hydroxyisosarcophytoxide-6-ene, and (+)-methyl cembra-1,3,7,11-tetraene-16-carboxylate have been isolated from Sinularia mayi, and their structures including the absolute configuration of 1 have been determined spectroscopically and by means of chemical reaction.

Yoshiharu Fujita

Papers

Anomaly in the modified Mosher's method: Absolute configurations of some marine cembranolides

New Cembranoids from the Okinawan Soft Coral Sinularia mayi